CA2747801A1 - Composes de sulfone heterocycliques satures n-substitues ayant une activite agoniste du recepteur cb2 - Google Patents

Composes de sulfone heterocycliques satures n-substitues ayant une activite agoniste du recepteur cb2 Download PDF

Info

Publication number: CA2747801A1
Authority: CA; Canada
Prior art keywords: alkyl; benzo; neopentyl; mmol; reaction
Prior art date: 2009-01-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA2747801A

Other languages

English (en)

Inventor

Kazuo Ando

Yasuhiro Iwata

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Raqualia Pharma Inc

Original Assignee

Raqualia Pharma Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2009-01-22

Filing date

2010-01-22

Publication date

2010-07-29

2010-01-22 Application filed by Raqualia Pharma Inc filed Critical Raqualia Pharma Inc

2010-07-29 Publication of CA2747801A1 publication Critical patent/CA2747801A1/fr

Status Abandoned legal-status Critical Current

Links

-1 saturated heterocyclic sulfone compounds Chemical class 0.000 title claims description 92
230000001270 agonistic effect Effects 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims abstract description 243
150000003839 salts Chemical class 0.000 claims abstract description 30
238000011282 treatment Methods 0.000 claims abstract description 20
230000000694 effects Effects 0.000 claims abstract description 18
102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims abstract description 17
108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims abstract description 17
230000001404 mediated effect Effects 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims description 72
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 48
125000000623 heterocyclic group Chemical group 0.000 claims description 46
125000000753 cycloalkyl group Chemical group 0.000 claims description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
125000001424 substituent group Chemical group 0.000 claims description 28
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
229910052757 nitrogen Chemical group 0.000 claims description 21
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
239000003814 drug Substances 0.000 claims description 16
150000002431 hydrogen Chemical group 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical group 0.000 claims description 14
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
208000002193 Pain Diseases 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
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229910052701 rubidium Inorganic materials 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
201000006474 Brain Ischemia Diseases 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
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206010008120 Cerebral ischaemia Diseases 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
PVXOUGHWLCBJOW-UHFFFAOYSA-N azetidine-1-carboxamide Chemical compound NC(=O)N1CCC1 PVXOUGHWLCBJOW-UHFFFAOYSA-N 0.000 claims description 5
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239000000460 chlorine Chemical group 0.000 claims description 5
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
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239000011737 fluorine Substances 0.000 claims description 4
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208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 claims description 3
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206010047115 Vasculitis Diseases 0.000 claims description 3
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
201000011510 cancer Diseases 0.000 claims description 3
201000007241 cutaneous T cell lymphoma Diseases 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
206010012601 diabetes mellitus Diseases 0.000 claims description 3
208000006454 hepatitis Diseases 0.000 claims description 3
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208000036971 interstitial lung disease 2 Diseases 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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OBFQWEKGLYLIJI-UHFFFAOYSA-N 1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-5-[(1-methylsulfonylazetidin-3-yl)methylsulfonyl]benzimidazole Chemical compound CC(C)(C)CC1=NC2=CC(S(=O)(=O)CC3CN(C3)S(C)(=O)=O)=CC=C2N1CC1CC1 OBFQWEKGLYLIJI-UHFFFAOYSA-N 0.000 claims description 2
CLRBOBWRXGOLHH-UHFFFAOYSA-N 1-[4-[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)benzimidazol-5-yl]sulfonyl-4-(hydroxymethyl)piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1(CO)S(=O)(=O)C1=CC=C(N(CC2CC2)C(CC(C)(C)C)=N2)C2=C1 CLRBOBWRXGOLHH-UHFFFAOYSA-N 0.000 claims description 2
NGISWPIKCIOFJD-UHFFFAOYSA-N 1-[4-[[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)benzimidazol-5-yl]sulfonylmethyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1CS(=O)(=O)C1=CC=C(N(CC2CC2)C(CC(C)(C)C)=N2)C2=C1 NGISWPIKCIOFJD-UHFFFAOYSA-N 0.000 claims description 2
GPTAFFHSWDOBMS-UHFFFAOYSA-N 2-[2-(2,2-dimethylpropyl)-5-(1-ethylazetidin-3-yl)sulfonylbenzimidazol-1-yl]-n,n-dimethylethanamine Chemical compound C1N(CC)CC1S(=O)(=O)C1=CC=C(N(CCN(C)C)C(CC(C)(C)C)=N2)C2=C1 GPTAFFHSWDOBMS-UHFFFAOYSA-N 0.000 claims description 2
WTHSZPNTEHZOLY-UHFFFAOYSA-N 2-[2-(2,2-dimethylpropyl)-5-(1-methylsulfonylazetidin-3-yl)sulfonylbenzimidazol-1-yl]-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=C2N(CCN(C)C)C(CC(C)(C)C)=NC2=CC=1S(=O)(=O)C1CN(S(C)(=O)=O)C1 WTHSZPNTEHZOLY-UHFFFAOYSA-N 0.000 claims description 2
MULJZWUIBNQHCI-ZEECNFPPSA-N 2-[2-(2,2-dimethylpropyl)-5-[(3r)-1-methylpyrrolidin-3-yl]sulfonylbenzimidazol-1-yl]-n,n-dimethylethanamine;dihydrochloride Chemical compound Cl.Cl.C=1C=C2N(CCN(C)C)C(CC(C)(C)C)=NC2=CC=1S(=O)(=O)[C@@H]1CCN(C)C1 MULJZWUIBNQHCI-ZEECNFPPSA-N 0.000 claims description 2
MULJZWUIBNQHCI-RMRYJAPISA-N 2-[2-(2,2-dimethylpropyl)-5-[(3s)-1-methylpyrrolidin-3-yl]sulfonylbenzimidazol-1-yl]-n,n-dimethylethanamine;dihydrochloride Chemical compound Cl.Cl.C=1C=C2N(CCN(C)C)C(CC(C)(C)C)=NC2=CC=1S(=O)(=O)[C@H]1CCN(C)C1 MULJZWUIBNQHCI-RMRYJAPISA-N 0.000 claims description 2
OAYGNQGEUIFBFA-UHFFFAOYSA-N 2-[3-[1-[2-(dimethylamino)ethyl]-2-(2,2-dimethylpropyl)benzimidazol-5-yl]sulfonylazetidin-1-yl]ethanol Chemical compound C=1C=C2N(CCN(C)C)C(CC(C)(C)C)=NC2=CC=1S(=O)(=O)C1CN(CCO)C1 OAYGNQGEUIFBFA-UHFFFAOYSA-N 0.000 claims description 2
XRDGNNFVPXTXMH-UHFFFAOYSA-N 2-tert-butyl-1-(cyclopropylmethyl)-5-[(1-methylsulfonylpiperidin-4-yl)methylsulfonyl]benzimidazole Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)CC3CCN(CC3)S(C)(=O)=O)=CC=C2N1CC1CC1 XRDGNNFVPXTXMH-UHFFFAOYSA-N 0.000 claims description 2
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KTPKWQLHEUWUOK-UHFFFAOYSA-N [4-[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)benzimidazol-5-yl]sulfonyl-1-methylsulfonylpiperidin-4-yl]methanol Chemical compound CC(C)(C)CC1=NC2=CC(S(=O)(=O)C3(CO)CCN(CC3)S(C)(=O)=O)=CC=C2N1CC1CC1 KTPKWQLHEUWUOK-UHFFFAOYSA-N 0.000 claims description 2
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125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 1
229960004010 zaleplon Drugs 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
229960001475 zolpidem Drugs 0.000 description 1
ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
229960003414 zomepirac Drugs 0.000 description 1
229960000820 zopiclone Drugs 0.000 description 1

Classifications

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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Pulmonology (AREA)
Biomedical Technology (AREA)
Physical Education & Sports Medicine (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Rheumatology (AREA)
Virology (AREA)
Oncology (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Orthopedic Medicine & Surgery (AREA)
Communicable Diseases (AREA)
Urology & Nephrology (AREA)
Ophthalmology & Optometry (AREA)
Otolaryngology (AREA)
Molecular Biology (AREA)
Hospice & Palliative Care (AREA)
Dermatology (AREA)
Vascular Medicine (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
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CA2747801A 2009-01-22 2010-01-22 Composes de sulfone heterocycliques satures n-substitues ayant une activite agoniste du recepteur cb2 Abandoned CA2747801A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US20203609P	2009-01-22	2009-01-22
US61/202,036		2009-01-22
US21397709P	2009-08-04	2009-08-04
US61/213,977		2009-08-04
PCT/JP2010/000377 WO2010084767A1 (fr)	2009-01-22	2010-01-22	Composés de sulfone hétérocycliques saturés n-substitués ayant une activité agoniste du récepteur cb2

Publications (1)

Publication Number	Publication Date
CA2747801A1 true CA2747801A1 (fr)	2010-07-29

Family

ID=42355822

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2747801A Abandoned CA2747801A1 (fr)	2009-01-22	2010-01-22	Composes de sulfone heterocycliques satures n-substitues ayant une activite agoniste du recepteur cb2

Country Status (10)

Country	Link
US (1)	US8653063B2 (fr)
EP (1)	EP2379533A4 (fr)
JP (1)	JP5816883B2 (fr)
KR (1)	KR20110117146A (fr)
CN (1)	CN102292328A (fr)
BR (1)	BRPI1007202A2 (fr)
CA (1)	CA2747801A1 (fr)
MX (1)	MX2011007663A (fr)
RU (1)	RU2011134868A (fr)
WO (1)	WO2010084767A1 (fr)

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Publication number	Priority date	Publication date	Assignee	Title
US9925282B2 (en)	2009-01-29	2018-03-27	The General Hospital Corporation	Cromolyn derivatives and related methods of imaging and treatment
WO2012090179A2 (fr)	2010-12-30	2012-07-05	Lupin Limited	Dérivés d'isoquinoline en tant que modulateurs des récepteurs cannabinoïdes
WO2012090177A2 (fr)	2010-12-30	2012-07-05	Lupin Limited	Modulateurs des récepteurs cannabinoïdes
CN102276511A (zh) *	2011-06-20	2011-12-14	兰州博实生化科技有限责任公司	1-叔丁氧羰基-3-碘氮杂环丁烷的合成方法
WO2013005168A2 (fr)	2011-07-05	2013-01-10	Lupin Limited	Modulateurs des récepteurs de cannabinoïdes
CN102432514B (zh) *	2011-12-26	2014-05-07	兰州博实生化科技有限责任公司	1-叔丁氧羰基-3-氟氮杂环丁烷的合成方法
US8633182B2 (en)	2012-05-30	2014-01-21	Boehringer Ingelheim International Gmbh	Indanyloxyphenylcyclopropanecarboxylic acids
EP3563849A3 (fr)	2012-10-25	2020-02-12	The General Hospital Corporation	Polythérapies pour le traitement de la maladie d'alzheimer et des troubles associés
US10525005B2 (en)	2013-05-23	2020-01-07	The General Hospital Corporation	Cromolyn compositions and methods thereof
CN110305095A (zh)	2013-10-22	2019-10-08	综合医院公司	色甘酸衍生物以及成像和治疗的相关方法
JP2019524865A (ja)	2016-08-31	2019-09-05	ザジェネラルホスピタルコーポレイション	神経変性疾患と関連する神経炎症におけるマクロファージ／ミクログリア
JP7202376B2 (ja)	2017-07-20	2023-01-11	エーゼットセラピーズ，インコーポレイテッド	クロモリンナトリウムおよびイブプロフェンの粉末製剤
AU2019299347A1 (en)	2018-07-02	2021-01-21	Aztherapies, Inc.	Powdered formulations of cromolyn sodium and alpha-lactose
MX2021006869A (es)	2018-12-10	2021-07-02	Massachusetts Gen Hospital	Esteres de cromolin y usos de los mismos.
WO2021207060A1 (fr)	2020-04-06	2021-10-14	The General Hospital Corporation	Méthodes de traitement d'états inflammatoires induits par des coronavirus
CN116322672B (zh) *	2020-11-12	2024-04-09	株式会社AskAt	2-[3-({1-[2-(二甲基氨基)乙基]-2-(2,2-二甲基丙基)-1h-1,3-苯并二氮唑-5-基}磺酰基)氮杂环丁烷-1-基]乙-1-醇的稳定盐和晶型
WO2022146914A1 (fr)	2020-12-28	2022-07-07	The General Hospital Corporation	Dérivés de cromolyne et leurs utilisations

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FR2751649B1 (fr) *	1996-07-26	1998-08-28	Adir	Nouveaux derives de benzimidazole, de benzoxazole et de benzothiazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
GB0222493D0 (en) *	2002-09-27	2002-11-06	Glaxo Group Ltd	Compounds
ES2318556T3 (es)	2004-11-02	2009-05-01	Pfizer, Inc.	Derivados de sulfonil bencimidazol.
DE602007009807D1 (de) *	2006-03-06	2010-11-25	Raqualia Pharma Inc	Sulfonylbenzimidazolderivate
ATE459352T1 (de)	2006-07-04	2010-03-15	Janssen Pharmaceutica Nv	Benzimidazol-cannabinoid-agonisten mit einer substituierten heterocyclischen gruppe
US8193369B2 (en)	2007-03-30	2012-06-05	Janssen Pharmaceutica Nv	Benzimidazole cannabinoid agonists
JP5544299B2 (ja)	2007-12-17	2014-07-09	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	フルオロアルキル置換ベンズイミダゾールカンナビノイドアゴニスト

2010
- 2010-01-22 CA CA2747801A patent/CA2747801A1/fr not_active Abandoned
- 2010-01-22 RU RU2011134868/04A patent/RU2011134868A/ru unknown
- 2010-01-22 BR BRPI1007202A patent/BRPI1007202A2/pt not_active IP Right Cessation
- 2010-01-22 US US13/145,439 patent/US8653063B2/en active Active
- 2010-01-22 WO PCT/JP2010/000377 patent/WO2010084767A1/fr not_active Ceased
- 2010-01-22 KR KR1020117018693A patent/KR20110117146A/ko not_active Withdrawn
- 2010-01-22 JP JP2011526737A patent/JP5816883B2/ja active Active
- 2010-01-22 CN CN2010800053579A patent/CN102292328A/zh active Pending
- 2010-01-22 EP EP10733374A patent/EP2379533A4/fr not_active Withdrawn
- 2010-01-22 MX MX2011007663A patent/MX2011007663A/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
KR20110117146A (ko)	2011-10-26
RU2011134868A (ru)	2013-02-27
MX2011007663A (es)	2011-08-15
EP2379533A1 (fr)	2011-10-26
CN102292328A (zh)	2011-12-21
US8653063B2 (en)	2014-02-18
US20110281840A1 (en)	2011-11-17
BRPI1007202A2 (pt)	2016-02-23
JP5816883B2 (ja)	2015-11-18
EP2379533A4 (fr)	2012-07-04
JP2012515712A (ja)	2012-07-12
WO2010084767A1 (fr)	2010-07-29

Legal Events

Date	Code	Title	Description
2014-03-20	FZDE	Discontinued	Effective date: 20140122

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